African American (AA) adolescents in an urban context experience significant mental health disparities compared to the national average, and they are overrepresented in the juvenile justice system. Mental health disorders among juvenile offenders (JO) are three times higher than community samples, yet JO on probation are unlikely to receive treatment. Exacerbating negative outcomes, JO report more risky sexual behavior, drug and alcohol use, and are more likely to test positive for STIs than non-offending youth. AA males are disproportionately involved in the juvenile justice system and particularly vulnerable to stress and poor health outcomes. This study will focus on males given that males overwhelmingly outnumber females in the juvenile justice system, especially males of color. Societal determinants, such racial discrimination, can negatively impact mental and physical health. However, the impact of perceived discrimination on young offenders' mental health outcomes is not well understood. Studies on perceived discrimination and other types of problem behaviors among youth offenders (substance use and risky sexual behavior) are virtually nonexistent. Moreover, the role of perceived discrimination is rarely addressed in prevention and intervention programs involving ethnic minority youth. Poor understanding of social stressors, such as perceived discrimination, may contribute to the lack of sustained prevention and intervention effects for AA JO. This analysis of secondary data will examine the impact of perceived discrimination on comorbity (mental health, substance use, and risky sexual behavior), and positive development (self-esteem and social competence) among African American male juvenile offenders in Chicago who participated in larger intervention study designed to reduce risky sexual behavior and substance use among JO in Chicago (R01MD005861; Donenberg, PI). Using a culturally informed theoretical framework, the proposed study will examine how resilience transpires among AA male JO, namely the protective and promotive value of both dispositional and event-specific coping and the protective and promotive value of cultural resources (e.g., ethnic-racial identity) on adjustment. Research on resilience is essential to understanding how these young men's developmental trajectories may be changed.